63279-13-0

Basic information

• Product Name: (4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester
• Synonyms: (4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester;Rebaudioside D;REBAUDIOSIDE C(P);(4alpha)-13-[(O-beta-D-Glucopyranosyl-(1-2)-O-[beta-D-glucopyranosyl-(1-3)]-beta-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl ester;(4α)-13-[(O-β-D-Glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid 2-O-β-D-glucopyranosyl-β-D-glucopyranosyl ester;Rebaudioside D (100 mg)
• CAS NO: 63279-13-0
• Molecular Formula: C50H80O28
• Molecular Weight: 1129.15
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 63279-13-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester(63279-13-0)
• EPA Substance Registry System: (4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester(63279-13-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 63279-13-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
(4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester is used as a potential therapeutic agent for various diseases due to its complex glycosidic structure and potential interactions with biological targets.
Used in Drug Delivery Systems:
In the field of drug delivery, this compound may be utilized as a component of novel drug delivery systems, taking advantage of its unique structural features to improve the bioavailability and targeting of therapeutic agents.
Used in Analytical Chemistry:
(4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester may serve as an internal standard or reference compound in the analysis of complex mixtures containing similar glycosylated compounds, such as those found in plant extracts or biological samples.
Used in the Food Industry:
As a nutritive sweetener, this compound may be used as a replacement for sugar in the food and beverage industry, particularly in products targeting consumers with diabetes, high blood pressure, or obesity, due to its non-caloric nature and potential sweetness.
Used in the Cosmetics Industry:
(4R)-13-[[2-O-(β-D-Glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]kaur-16-en-18-oic acid 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester's unique structure and properties may also find applications in the cosmetics industry, where it could be used as an active ingredient in skincare or hair care products, potentially offering moisturizing, anti-aging, or other beneficial effects.

Preparation

The rebaudioside D-rich steviol glycoside preparation (~95% rebaudioside D) is produced via an enzymatic conversion process using a strain of Pichia pastoris that has been genetically modified to express UDPglucosyltransferase EUGTll. In the first stage of manufacturing, a steviol glycoside primary extract from the leaves of 5. rebaudiana Bertoni containing 55±5% of rebaudioside A is produced according to the methodology outlined in the Chemical and Technical Assessment (CTA) published by the Food and Agriculture Organization (FAO)/JECFA for steviol glycosides (FAQ, 2016). In the next step, the steviol glycoside primary extract is further purified to a purity of ~95% rebaudioside A through crystallization, also consistent with the CTA methodology. In the third stage, the P. pastoris production strain is subjected to a fermentation step to express the UGT-glucosyltransferase EUGTll, which is used to catalyze the conversion of the high-purity rebaudioside A extracted from 5. rebaudiana Bertoni to rebaudioside D. In the last stage, the rebaudioside D solution is purified and concentrated according to the methodology described in the steviol glycoside CTA, yielding a final product that contains ~95% rebaudioside D.www.fda.gov

Upstream product

• 57-50-1 Sucrose 
• 133-89-1 UDP-glucose 
• 64849-39-4 13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol 
• 57817-89-7 stevioside 
• 20880-64-2 sophorose 
• 58543-17-2 rebaudioside B 
• 58543-16-1 rebaudioside A 

Downstream Products

• 1220616-44-3 13-[(2-O-(β-D-glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-(β-D-glucopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester 

Relevant articles and documents

Diversity-Oriented Synthesis of Steviol Glycosides

With cheap and easily available mixtures of steviol glycosides as starting materials, a practical method for steviol acquisition has been developed, on the basis of which a facile, diversity-oriented, and economic protocol for the synthesis of structurally defined steviol glycosides was established. The novel approach is featured by the highly efficient glycosylation of sterically hindered and acid-sensitive steviol via orchestrated application of Yu glycosylation, Schmidt glycosylation, and PTC glycosylation. Hence, these high-intensity sweeteners and potential lead compounds for drug development are now readily accessible.

Method of converting RB to RD by using cutinase under stepwise changing temperatures

The present invention provides a method to produce RD by using a cutinase to catalyze the esterification of RB under stepwise cooling temperatures, which is related to the field of biosynthesis of organic compounds. The method uses a cutinase from Thermobifida fusca to catalyze the esterification of RB and sophorose to produce RD. The stepwise cooling temperatures are used to reduce the heat inactivation of the enzyme as well as to improve the mass transfer. The method catalyzes the esterification of RB to produce RD in a solvent such as methanol, DMSO and DMF. The reaction is safe, efficient and highly selective. In addition, the method uses stepwise additions of substrate RB and cooling temperatures for the esterification reaction. In this way, it speeds up the initial reaction rate, increases the amount of solved RB as it is converted to RD, and improves the mass transfer to further increase the reaction speed. In summary, the method uses moderate reaction conditions, and has a high yield and a simple purification procedure.

HIGH-PURITY STEVIOL GLYCOSIDES

Methods of preparing highly purified steviol glycosides, particularly rebaudiosides A, D and M are described. The methods include utilizing recombinant microorganisms for converting various staring compositions to target steviol glycosides. In addition, novel steviol glycosides reb D2, reb M2, and reb I are disclosed, as are methods of preparing the same. The highly purified rebaudiosides are useful as non-caloric sweetener in edible and chewable compositions such as any beverages, confectioneries, bakery products, cookies, and chewing gums.

PRODUCTION OF STEVIOL GLYCOSIDES IN RECOMBINANT HOSTS

The invention relates to recombinant microorganisms and methods for producing steviol glycosides, glycosylated ent-kaurenol, and glycosylated ent-kaurenoic acid.

RECOMBINANT PRODUCTION OF STEVIOL GLYCOSIDES

Recombinant microorganisms, plants, and plant cells are disclosed that have been engineered to express recombinant genes encoding UDP-glycosyltransferases (UGTs). Such microorganisms, plants, or plant cells can produce steviol glycosides, e.g., Rebaudioside A and/or Rebaudioside D, which can be used as natural sweeteners in food products and dietary supplements.

HIGH-PURITY STEVIOL GLYCOSIDES

Methods of preparing highly purified steviol glycosides, particularly rebaudiosides A, D and M are described. The methods include utilizing recombinant microorganisms for converting various staring compositions to target steviol glycosides. In addition, novel steviol glycosides reb D2 and reb M2 are disclosed, as are methods of preparing the same. The highly purified rebaudiosides are useful as non-caloric sweetener in edible and chewable compositions such as any beverages, confectioneries, bakery products, cookies, and chewing gums.

Novel Process for the Preparation of Rebaudioside D and Other Related Naturally Occurring Sweetners

A novel process for preparation of Rebaudioside D (RD), and other related naturally occurring sweeteners is provided. RD is a natural sweetening agent which can decrease the bitter aftertaste of steviol glycosides. The said process is suitable for commercial manufacturing by using readily available natural products and nontoxic reagents.